Z-Gly-Pro-Leu-Gly | 2646-64-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Z-Gly-Pro-Leu-Gly
• 英文别名: Cbz-Gly-L-Pro-L-Leu-Gly-OH；2-[[(2S)-4-methyl-2-[[(2S)-1-[2-(phenylmethoxycarbonylamino)acetyl]pyrrolidine-2-carbonyl]amino]pentanoyl]amino]acetic acid
• CAS: 2646-64-2
• 化学式: C₂₃H₃₂N₄O₇
• 分子量: 476.53
• InChiKey: BHYBKKFGHQVXFO-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Z-Gly-Pro-Leu-Gly 在 N-甲基吗啉 、 氢溴酸 、 氯甲酸异丁酯 作用下， 以 溶剂黄146 为溶剂， 反应 6.58h， 生成 glycyl-L-prolyl-L-leucylglycine anilide
  参考文献：
  名称：

  Moir, Michael E.; Crawford, Robert J., Canadian Journal of Chemistry, 1988, vol. 66, p. 2903 - 2913

  摘要：

  DOI：

文献信息

• Substrate-Directed Lewis-Acid Catalysis for Peptide Synthesis
  作者：Wataru Muramatsu、Tomohiro Hattori、Hisashi Yamamoto

  DOI：10.1021/jacs.9b03850

  日期：2019.8.7

  A Lewis-acid-catalyzed method for the substrate-directed formation of peptide bonds has been developed, and this powerful approach is utilized for the new "remote" activation of carboxyl groups under solvent-free conditions. The presented method has the following advantages: 1) the high-yielding peptide synthesis uses a tantalum catalyst for any amino acids; 2) the reaction proceeds without any racemization;

  一种路易斯酸催化的底物定向形成肽键的方法已经被开发出来，这种强大的方法被用于在无溶剂条件下对羧基进行新的“远程”活化。该方法具有以下优点：1）高产肽合成对任何氨基酸均使用钽催化剂；2) 反应进行时没有任何外消旋化；3）采用钛催化剂的新型底物导向化学连接适用于会聚肽合成。这些优势克服了经典肽合成中一些未解决的问题。
• Propargyl-Assisted Selective Amidation Applied in C-terminal Glycine Peptide Conjugation
  作者：Kenward King Ho Vong、Satoshi Maeda、Katsunori Tanaka

  DOI：10.1002/chem.201604247

  日期：2016.12.23

  nucleophilic acyl substitution reactions. Herein, we report an unusual observation in which glycine propargyl ester derivatives displayed selective, base‐independent reactivity towards linear alkylamines under mild, metal‐free conditions. Through global reaction route mapping (GRRM) modeling calculations, it is predicted that these observations may be governed by factors related to hydrogen‐bonding and intermolecular

  烷基酯（例如炔丙基酯）通常缺乏参与亲核酰基取代反应所需的吸电子诱导效应。在此，我们报告了一个不寻常的观察结果，其中甘氨酸炔丙基酯衍生物在温和，无金属的条件下对线性烷基胺表现出选择性的，与碱无关的反应性。通过整体反应路线图（GRRM）建模计算，可以预测这些观察结果可能受与氢键和分子间相互作用相关的因素的支配，而不是由吸电子的感应效应支配。基于炔丙基辅助选择性酰胺化的概念，直接开发了一种新的位点特异性C末端甘氨酸肽生物缀合技术作为概念验证，
• Action on peptides by wheat carboxypeptidase
  作者：H. Umetsu、E. Ichishima

  DOI：10.1016/0031-9422(83)83054-4

  日期：1983.1

  Abstract A kinetic analysis has been performed with purified wheat carboxypeptidase by the use of N -acyl dipeptides, Z-Gly-Pro-Leu-Gly (Z = benzyloxycarbonyl), angiotensin II and bradykinin. The values of k cat were dramatically influenced by amino acid residues occupying the penultimate position from the carboxyl terminus of substrates. The structure of the substrate did not appreciably affect the

  摘要 使用 N-酰基二肽、Z-Gly-Pro-Leu-Gly（Z = 苄氧羰基）、血管紧张素 II 和缓激肽对纯化的小麦羧肽酶进行了动力学分析。k cat 的值受到占据底物羧基末端倒数第二个位置的氨基酸残基的显着影响。底物的结构对 K m 值没有明显影响。
• Affinity chromatography of alkaline proteinase S on N-carbobenzoxyglycylleucylaminohexyl-Sepharose.
  作者：YOSHIO INOUYE、SHOSHIRO NAKAMURA、MASA HAMADA、KAZUO AIKAWA、KANSHIRO KITAGAKI、KAZUNORI SATO、EIICHI YASUDA

  DOI：10.1248/cpb.32.4036

  日期：——

  Alkaline proteinase produced by one of the monospore isolates of Streptomyces violaceorectus MC675-A8, a producer of the alkaline metalloendopeptidases named alkinonases A and AF, was purified by affinity chromatography on N-benzyloxycarbonylglycylleucylaminohexyl-Sepharose to electrophoretic homogeneity. The enzyme was inactivated by phenylmethanesulfonyl fluoride and diisopropylfluorophosphate, but not by chelating agents or sulfhydryl reagents, and was distinct from alkinonases A and AF. The optimum pH for casein hydrolysis was 9.5-10.5, and the enzyme was stable within a pH range of 5.0-12.0. The molecular weight was estimated to be 30000. The peptidase activity of the enzyme was greatest on N-benzyloxycarbonylglycylprolylleucylglycine ethyl ester among the synthetic substrates tested in this work. Amidase activity was observed towards peptide amides such as N-benzyloxycarbonylglycylleucine amide and N-benzyloxycarbonylglycylphenylalanine amide. The enzyme showed anti-inflammatory activity against carrageenan-induced edema in rats, as did alkinonases A and AF. Bradykinin was hydrolyzed by the enzyme to arginylprolylprolylglycylphenylalanylserylprolylphenylalanine and arginine. Since the enzyme showed a serine proteinase nature, the enzyme was named alkaline proteinase S, and the producing microbe was designated as Streptomyces violaceorectus MC675-A8-S.

  紫色直肠链霉菌 MC675-A8 的单孢子分离株之一产生的碱性蛋白酶，它是名为阿激酶 A 和 AF 的碱金属内肽酶的生产者，通过 N-苄氧基羰基甘氨酰氨基己基-琼脂糖凝胶上的亲和层析纯化至电泳均质。该酶可被苯甲磺酰氟和二异丙基氟磷酸酯灭活，但不会被螯合剂或巯基试剂灭活，并且与羟激酶 A 和 AF 不同。酪蛋白水解的最适pH为9.5-10.5，酶在pH 5.0-12.0范围内稳定。分子量估计为30000。在本工作测试的合成底物中，该酶对N-苄氧基羰基甘氨酰脯氨酰甘氨酸乙酯的肽酶活性最大。观察到针对肽酰胺例如N-苄氧基羰基甘氨酰亮氨酸酰胺和N-苄氧基羰基甘氨酰苯丙氨酸酰胺的酰胺酶活性。该酶对角叉菜胶引起的大鼠水肿具有抗炎活性，羟激酶 A 和 AF 也具有同样的效果。缓激肽被酶水解成精氨酰脯氨酰甘氨酰苯丙氨酰丝氨酰脯氨酰苯丙氨酸和精氨酸。由于该酶显示出丝氨酸蛋白酶性质，因此将该酶命名为碱性蛋白酶S，并且将产生微生物命名为Streptomyces violaceorectus MC675-A8-S。
• JPS5618948A
  申请人：——

  公开号：JPS5618948A

  公开（公告）日：1981-02-23